Dressed For Success
by Ralyena Starrling
Summary: Dark and Daisuke go out on a date while the red-head's parents are out of town. But there's a hitch on Dark's part: Daisuke has to wear a dress! This is gift for my friend DarkAngel048


Hello, everyone! This is my first Dark/Daisuke fic and a birthday present for my friend DarkAngel048. I hope you like it!

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"Come on Dai-chan, please wear it!"Dark begged in a whinny voice as he scratched at the door of his love's bedroom.

"No! I'm not going to embarrass myself by wearing that!"Daisuke stated in an embarrassed tone but it still held the finality he wanted it to have.

You see since Daisuke's parents are now out of town Dark figured that it would be a good chance to take Daisuke out on a date. When he told his young red-headed boyfriend his plan Daisuke was of course delighted. However there was a slight hitch. And what was this hitch?

Daisuke had to wear a dress, accessories and all. Then naturally after hearing that and seeing the dress Daisuke swiftly protested which led to him being chased by the purple-haired thief until he locked himself in his room.

"But Daisuke, you said that you'd do anything to make me happy."Dark said in a sad voice.

"How could me wearing something made for girls make you happy?"Daisuke asked in an outraged tone.

"Because you would look so cute in it, Dai-chan."Dark said in a sweet voice. Daisuke blushed and looked down at his clenched hands squeezing his shirt out of nervousness. Maybe it wouldn't be so bad wearing the dress. The red-head immediately shook the thought out of his head. No way! Just because he _looked_ feminine didn't mean that he had to dress like a girl! And he wouldn't!

"Forget it, Dark! I'm not wearing that thing and that's that!"Daisuke stated harshly and surprisingly managed to pull it off. He heard Dark sigh on the other side of the door.

"I see. So nothing's going to change your mind?"Dark asked.

"No!"Daisuke said in a stern tone. Then suddenly all that courage dropped down when he heard Dark chuckle, well, darkly.

"In that case, I suppose I'll have to use my trump card."Dark said in an evil, scheming tone. Daisuke gulped a little at what Dark said.

"Wh-What's your trump card?"Daisuke asked nervously, half curious half not wanting to know.

"Oh, nothing. I'll just sign you up for the female lead of your next school play is all."Dark said simply as if he was talking about the weather.

Daisuke gasped loudly and dreaded the thought of having to go through another play as the female lead. The unwanted attention, the heavy amounts of make-up….it was all Hell!

"No! You wouldn't dare, Dark!"Daisuke exclaimed hoping that his boyfriend was bluffing. All he got was a chuckle until Dark said,

"Try me."Dark said in a sing-song voice, checking his nails.

Daisuke bit his lower lip and growled in annoyance. He weighed his options. True he would have to cross-dress in both scenarios but in option two he would have to wear girl's clothes for a whole month until the play was over. In option one though he would only have to wear the dress for one night. With a deep sigh Daisuke answered,

"Fine. I'll wear the dress for tonight."Daisuke said in a defeated tone.

"Thank you, Daisuke! I'll send it up to you by Towa! We leave at nine! I need to go and set things up for our date. Don't forget now!"And with that said Dark ran down the stairs and out the door to set things up for tonight.

"Trust me, it'll be hard _not_ to remember selling my dignity to the Devil."Daisuke said to himself and sighed very regrettably.

While Dark was out setting things up Towa was helping Daisuke style his hair, put on his accessories and most importantly put on the dress. And as surprising as it was all that took four hours in total, but they finally finished Daisuke's make-over and it would be nine o'clock in four minutes.

"Oh, Dai-chan you look so lovely! I wish I had a dress like yours!"Towa said in a giddy voice with a wide smile. Daisuke chuckled a bit at the compliment.

"Thank you, Towa-kun."Daisuke said.

The dress actually looked very nice on the red head despite the fact that he was a boy. It was teal in color, the sleeves were long and the hem had a cream floral pattern which stopped above his knees. The shoes were cream colored medium-heeled sandals. His hair was neatly brushed back and the right side of his bangs were clipped up with a lavender dragonfly hairclip while his left side of bangs flowed in his face. He had two lavender bracelets on each wrist and a simple lavender beaded necklace. All in all Daisuke looked very sublime. The red-head blushed cutely and struggled to pull the hem down further.

"Dai-chan don't do that! You'll rip the hem!"Towa scowled. Daisuke flinched and let the hem go.

"Sorry, Towa-kun. But I'm just so embarrassed to wear this dress. What will other people say?"Daisuke asked in a cute nervous and worried tone. Towa only smiled.

"Don't worry about a thing, Dai-chan. If someone picks on you then Dark will surely teach them a lesson."Towa reassured. Daisuke smiled and giggled at the thought knowing that Towa was right. Then the door bell rang.

"Oh, that must be Dark! Come on Dai-chan!"Towa said eagerly and led Daisuke to the door.

Once the two were at the door Towa opened it and they saw a very handsome looking Dark.

The thief was wearing a royal purple button up long-sleeved shirt, dull grey jeans, a grey dress vest and black shoes. He combed his hair in a tamer look. Needless to say Dark was very handsome. The thief gracefully bowed and said,

"Good evening, Miss Towa. I'm here to take my lovely Daisuke out for a date."Dark stated in a polite tone and looked up at the white-haired woman with a charming smile. Towa chuckled while Daisuke blushed.

"Of course, Dark. Here he is!"Towa said and stepped out of the way so the purple-haired male could see Daisuke. The red-head looked at Dark nervously with a very deep blush on his face.

"H-Hello, Dark."Said the blushing male with a small smile. Dark grinned and took Daisuke's hand before giving it a small kiss which made the young red-head blush even more if that was possible.

"Hello, my sweet Dai-chan. Are you ready?"Dark asked charmingly. Daisuke was a bit chocked on words until he said,

"Yes. Let's go."Daisuke said with a wider smile. Dark nodded and grabbed Daisuke's white coat hanging on the rack and placed it around his lover's shoulders so gently that you'd think he was wrapping up a fragile gem.

"Let's be on our way then. Don't wait up, Towa."Dark said and the two walked out the door.

"Have fun, you two!"Towa called out as she waved the two lovers off once they drove away.

Dark was driving down the road smoothly in his silver sports car, a Corvette to be exact. The ride down the road was quiet mainly because Daisuke was too nervous to say anything. It was only until ten minutes passed did the younger male speak.

"So where are we going?"Daisuke asked truly curious about where his boyfriend was taking him.

"It's a surprise. But don't worry, you'll enjoy every minute of it."Dark said and gave a wink to Daisuke. The red-head blushed and looked away.

Soon Dark pulled over to a fancy five star restaurant. Daisuke looked up at the sign and saw that it said **"**_**Palm Leaves Bistro".**_

"Palm Leaves Bistro? I've never heard of this restaurant before."Daisuke said.

"It's a new French restaurant that opened up a few weeks ago. It's really popular and serves all kinds of delicious foods. Plus they even make your favorite dessert."Dark said and Daisuke's eyes lit up with happiness.

"Really? Oh, thank you Dark. That's so sweet of you."Daisuke said with a wide smile which made Dark smile as well.

"Anything for you, my little angel. Now let's go inside."Dark said and got out the car then went around and opened Daisuke's door and the gesture made him blush.

"I could open my own door, Dark. I'm not a girl you know."Daisuke said and took the hand Dark offered.

"_Could have fooled me."_Dark thought with a grin as they walked into the restaurant.

The lovers were brought to their table which was at the far end of the restaurant. As they were led to their table people were looking at Daisuke and Dark. Or rather people were looking more at Daisuke. Men looked at him with a lust that was more than noticeable and women looked at him with jealousy that was also easy to notice. The younger of the two started to feel really nervous and unintentionally gripped Dark's hand harder for reassurance. Dark got the hint and gently squeezed Daisuke's hand back.

"Relax, Dai-chan. I won't let any of these perverted men or jealous women touch you."Dark said in an assuring tone and brought the cream skinned hand to his mouth giving it a gentle kiss. Daisuke blushed a little and smiled.

A waiter came over and took their orders then left to get their food. After ten minutes their dinner came. Dark's plate had a well done steak with mashed potatoes and green peas and Daisuke's plate had teriyaki chicken in salad with mandarin oranges.

"I hope you enjoy your dinner, Sir and Madam. Is there anything I can get for you, Miss?"The waiter asked and leaned in a bit too close for Daisuke's comfort which made him move back a little.

"Uh, no. That's all thank you."Daisuke said with a shy smile but the waiter didn't relent and leaned in closer.

"Surely there must be something you want."The waiter said and nearly touched the nervous red-head's lips but he was pulled back by the collar of his shirt and faced with a very angry looking Dark Mousy. His eyes were glowing with rage and he had a deep scowl on his face.

"The lady said no. So I suggest you go somewhere else and serve someone else. Understand?"Dark asked in a cold low tone. The waiter shook with fear and nodded slowly. Dark let him go and the young man ran off without a word. The thief then gracefully sat back down in his chair and started to eat.

"Thank you, Dark."Daisuke said in a grateful tone.

"Not a problem at all, Dai-chan. I couldn't just let some pervert touch you and get away with it."Dark said and the couple continued eating.

After finishing dinner and having a strawberry topped chocolate cake for dessert the two left the restaurant and just as Daisuke sat down on his seat in the car a cloth was placed over his eyes.

"Ah! What's happening?"The red-head asked in shock.

"Relax my angel, it's me. I'm taking you to another special place but it's a big surprise and I want to make sure that you don't peek."Dark said and gave a kiss to Daisuke's cheek. Relaxing a little the younger male nodded and let Dark finish tying the blind fold over his eyes. Then the couple once again got into the car and drove off.

The ride to this new location was just as silent as the ride to the restaurant. Daisuke shook on the inside with eagerness at the thought of what this next surprise could be. He could only imagine and knowing Dark it wouldn't be anything too short of amazing. The car came to a stop and Daisuke heard the car door open and figured that Dark got out the car. Then his own door was opened and a strong but gentle hand grabbed onto his hand and pulled Daisuke out of the car. The couple were in the woods where there was a large cabin waiting for them.

"Here we are, my hikari. This is something that I've been working on for a long time and I hope that you'll enjoy it."Dark said sweetly and led Daisuke further to the cabin . Daisuke nearly tripped when he came to the stairs but Dark helped him along. He heard the jingle of a pair of keys, the jiggle of a knob twisting and the creak of a door being opened. Daisuke was about to ask the thief what was going on until he was immediately lifted up from the floor and held in his boyfriend's arms like a bride. So rather than actual words a squeak came out of the red-head's mouth.

"Dark what are you doing?"Daisuke asked in a shocked tone.

"Relax, Daisuke. I'm just taking you to your surprise. Or rather _our _surprise."Dark said and walked up the stairs with a blushing uke in his arms.

Dark walked into the bedroom and gently laid his innocent love on the soft satin bed. He loomed over Daisuke and took the cloth off his eyes. Daisuke blinked his eyes a few times and then saw Dark looming over him and started to grow a bit uncomfortable.

"D-Dark? Wh-What are you doing?"Daisuke asked in a small voice. Dark smiled lovingly at the nervous boy and kissed his forehead before he nuzzled his neck.

"What I'm doing, my sweet hikari, is giving you your surprise. I have been waiting for this chance for a long time and now that I have it I don't wish to stop….Daisuke, I want to make love to you. I want to hear you moan and shout my name as I give you massive amounts of pleasure. I want our bodies to be bound together in the closet way possible. So all I ask is, will you let me do these things?"Dark asked in a charming, caring voice.

Daisuke looked up at him with wide eyes. Dark wanted to make love with him? He always figured that they would do this eventually in the whole two and a half years they've been together. And it wasn't that he wouldn't want to make love with his boyfriend or anything like that. He was just very nervous. Daisuke was silent for a long time until he finally gave an answer.

"Do you….do you promise you'll be gentle?"Daisuke asked in a sweet nervous tone. Dark let out a breath of relief and smiled even more. He leant down and gave his lover a deep, passionate kiss. Daisuke moaned into the kiss and held onto the broad shoulders of his love. Dark broke the kiss and then replied,

"Yes, I'll be as gentle as you want. And if you ever want to stop we can. I promise you."Dark said and laid gentle kisses all over Daisuke's face. The boy giggled at the feel of the kisses and gave a few kisses of his own to Dark's cheeks.

Then Dark sat up on his knees for a moment to take off his vest and shirt and his red-head blushed at the sight of his uncovered chest and closed his eyes then put his hands over them. Dark chuckled and gently grasped the small hands and kissed the uke on his hands.

"Come now, Dai-chan. There's no need to be embarrassed. You'll be seeing me naked in a moment as I'll be seeing you undressed. Relax and enjoy it. Keep your eyes open. I want you to feel _and _see the pleasure I'm about to give you."Dark said softly. Daisuke whimpered but opened his eyes anyway. Dark smiled and continued with his ministrations.

He first took off Daisuke's jewelry and hairclip and set them down on the nightstand. Then he gently took off the heels and set them on the hardwood floor. Dark grabbed onto Daisuke's thigh firmly and slid his hand up and down the slender thigh.

"Ah! D-Dark….don't….stop….ahh."Daisuke moaned out helplessly and Dark grinned.

The thief continued to move his hand up and down and even squeezed onto the more sensitive parts of his leg and moved his free hand to the other leg and did the same. Daisuke was very enthralled in the pleasure. He was panting softly and had a deep unrelenting blush on his face and struggled to keep his lust hazed eyes open.

Though Daisuke was swamped by the feelings of mass pleasure he wasn't too out of it not to feel hands on the lacy powder blue panties he was forced to wear. Daisuke gasped in shock and sat up on his elbows to look at Dark and see the hem of his dress pushed up and Dark was looking at his crotch with a tender face as his strong hands pulled off the panties. Daisuke whimpered a bit fearfully and bit the back of his hand to pipe down his scared whimpering but Dark heard it and looked up at the boy. He saw the blush and emotions of love, nervousness and slight fear all over his face. Dark smiled loving again and moved up to kiss his lover.

"Relax, Daisuke. I promised I would be gentle and I will. I know that you must feel nervous and a little scared but this will all be worth it once you feel the immense pleasure to come. Okay?"Dark asked gently. Daisuke smiled a bit at the kind words offered and nodded. Dark smiled and took the small lips and kissed his love deeply again.

As the uke moaned into the kiss Dark took the chance to move his free hand under the pillow and got hold of a bottle of lube then twisted the cap off and poured some onto his fingers. He moved his slicked fingers down to Daisuke's lower half and pulled the panties off the rest of the way. With the small garment out of the way the seme moved his fingers to push past the soft cheeks of Dai's rear and circled his index finger around the ring of muscle. Daisuke of course felt this and gasped at the cold feeling and broke the kiss to look at his lover.

"What's that? What are you doing, Dark?"Daisuke asked in a very shocked voice. His lover gave him another tender kiss and said,

"I'm preparing you of course. If I don't you'll get hurt from what is to come next and I don't want that. Calm down and just enjoy this."Dark said and placed his lips on a vein of Daisuke's neck and suckled it gently and soothingly. This calmed down the young male and he laid his head back on the pillow, letting Dark go on with preparing him.

Dark finally pushed his finger into the anus of his soon-to-be-lover and groaned a bit at how tight and hot it felt. Dark held back the urge to simply shove his shaft into Daisuke knowing that it would hurt his love without proper preparation. The red-head whimpered in slight pain and moaned softly in pleasure. The seme then added another finger and began a scissoring motion. The younger male gave a long soft groan though his boyfriend couldn't tell if it was out of pain or pleasure. Taking a guess the purple-haired male lightly touched a random spot inside of his love and got a wonderful reaction.

Daisuke's eyes went as wide as they could get and he gave a _very _loud moan and bucked his hips. He felt an amazing spike of pleasure rush through him when Dark touched that spot in him. It was so intense it was almost painful but it still felt amazing. So amazing that he came and shot his fluids onto both Dark's bare chest and his dress. Daisuke got off on his lust high and laid back down onto the bed panting heavily all the while. Dark smiled at his angel. How he loved Daisuke's reaction to the feel of his prostate being touched. It was such a raw, powerful reaction to see. Something that he never saw in the previous lovers he had in his old life.

"Did you like how that felt, my love?"Dark asked both sweetly and teasingly at the same time.

"Yes! Please do that again! Please!"Daisuke begged in a pleading voice and his lover was only too happy to oblige. He jabbed at the spot harder while stretching out the small hole. And in return for the pleasure Dark received loud moans either begging for more or chanting his name.

"_This is better than I'd hope it would be. He's a real screamer for such a shy one."_Dark thought to himself and felt his shaft get harder and harder. Deciding that it was time Dark pulled his fingers out and pulled off the dress on his lover and tossed it somewhere on the floor and then did the same with his pants. Daisuke was about to ask Dark why he took his fingers out until he saw the desperate look of lust on his face which made the words stop in his throat. The purple haired male moved in between the red-head's thighs and grabbed the lube again then slicked up his rock hard shaft. He knelt down and gave a rough kiss to the now swollen lips of his angel and broke the kiss just as quickly as he gave it. Dark gave Daisuke a lustful grin before he said anything.

"Sorry, Dai-chan. But I can't hold back anymore. Are you ready?"Dark asked in as sweet a voice he could manage but it came out in lustful, desperate tone. Daisuke giggled at the tone of voice his lover had and wrapped his arms around his lover's neck and gave him a chaste kiss on the lips. He looked at the lustful seme with his own hazed-over look and said,

"Yes. Take me now."Daisuke said with a small seductive smile. The thief grinned and began his eager but otherwise slow penetration.

He pushed past the stretched out ring of muscle and Daisuke gave a whimper of discomfort but made no move to stop his boyfriend. Dark pressed in further and thought for a moment on where Daisuke's prostate was. When he remembered he angled the tip of his shaft to that area and made a swift plunge at it. Once again Daisuke saw stars and screamed in pleasure. After that Dark needed no further instructions on what to do.

The purple-haired male made slow hard thrusts at Daisuke's sweet spot. At times he would go faster but then would go slow again. Daisuke moaned in pleasure as Dark thrust inside him.

"Oh, Dai-chan. You're so tight and warm. I love you so much."Dark said and kissed his lover on the cheek. Daisuke looked up at him with red eyes shining brightly and smiled.

"I love you too, Dark. I love you very much."Said Daisuke and he leaned up then kissed his lover deeply. Dark returned the kiss and continued to make love to his angel.

Feeling Daisuke tighten around him Dark grabbed onto his lover's neglected member and pumped it in time with his thrusts which were getting faster.

"Dark! I….I'm going to….!"Daisuke tried to finish his sentence but all that came out were moans.

"I know, Dai-chan. Let's come together."Dark said and continued to pleasure his lover.

Soon the heat building up in their stomachs became too much and the two lovers ejaculated in unison.

"Dark!"Daisuke shouted in pleasure.

"Daisuke!"Dark shouted with him.

They both came hard until they were completely spent. Their pleasure high was brought down to zero and they panted harshly to catch their breath. Dark removed himself from Daisuke's body which earned him a sad groan. The thief chuckled and pulled the blankets over him and Daisuke. The young boy yawned in sleepiness and cuddled into his love's strong chest.

"That was wonderful, Dark. I really enjoyed myself tonight."Daisuke said in a sincere tone. Dark smiled widely and wrapped his arms around his lover.

"I did also, my angel. I love you with all my heart."Dark said and kissed the top of Daisuke's forehead.

"And I love you, too."Daisuke said and snuggled closer into Dark's chest.

There was a long silence and just as Daisuke was about to fall asleep Dark nudged at him.

"Hey, Daisuke? Can I ask you a question?"Dark asked.

"What is it?"Daisuke asked in a sleepy tone.

"Since you didn't hate wearing the dress for our date, would you be willing to wear dresses on all of our dates from now on?"Dark asked with a hopefully look while Daisuke looked at him as if the older male had grown horns and a second head.

Needless to say after that question, Dark was sleeping in the cold living room on the couch and it didn't seem a like another date would be coming up anytime soon.

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And that's it! I hoped you all enjoyed the story. Also a Jigen/Goemon one-shot will be made and posted for all of you to see. So until then bare with me. Take care!


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